Ethyl Acetate → HCID 66775565, compound

HRID 1645183Notes

Reaction equation

HRID 1645183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl.C(OCC)(=O)C>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 23392Picolyl chloride hydrochlorideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 66775565HCID 66775565, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Under a nitrogen atmosphere: to a solution of 1H-indole-6-carboxylic acid methyl ester (for synthesis see example 2a), 2.47 g, 14.1 mmol) in NMP (140 mL) was added Cs2CO3 (10.1 mg, 31 mmol) at 0° C. After stirring for 15 min 2-picolyl chloride hydrochloride (2.77 g, 16.9 mmol) was added and the mixture was stirred at room temperature for 18 h. Ethyl acetate (200 mL) was added and the mixture was washed with saturated aqueous ammonium chloride (3×150 mL) and brine (200 mL). The organic phase was dried (Na2SO4) and concentrated. The crude product was purified using column chromatography (ethyl acetate/heptane 1:3) to give the title compound as a colourless oil, which slowly crystallised on standing (2.72 g, 10.2 mmol, 72%).

Workup

  1. additionwas added
  2. washthe mixture was washed with saturated aqueous ammonium chloride (3×150 mL) and brine (200 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-b9eb1fd8c7b243db9c185f56789ef60b
Source dataset
uspto-grants-2012_02
Patent number
US08124647B2

Reaction notes

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